Triethylamine → 5-Bromo-6-cyclopropyl-3-((trimethylsilyl)ethynyl)pyridin-2-amine

HRID 531446Notes

Reaction equation

HRID 531446 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](I)[C:5]([NH2:11])=[N:6][C:7]=1[CH:8]1[CH2:10][CH2:9]1.C(N(CC)CC)C.[C:20]([Si:22]([CH3:25])([CH3:24])[CH3:23])#[CH:21]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:21]#[C:20][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:5]([NH2:11])=[N:6][C:7]=1[CH:8]1[CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 900227685-Bromo-6-cyclopropyl-3-iodopyridin-2-amine

Product 1

HCID 900223295-Bromo-6-cyclopropyl-3-((trimethylsilyl)ethynyl)pyridin-2-amine

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Cuprous iodide (11.23 mg, 0.059 mmol) was added to a mixture of 5-bromo-6-cyclopropyl-3-iodopyridin-2-amine (1 g, 2.95 mmol), triethylamine (13.4 g, 132.75 mmol) and THF (4 mL) and the resultant mixture was purged with nitrogen gas. Ethynyltrimethylsilane (347.7 mg, 3.54 mmol) and Pd(PPh3)2Cl2 (41.36 mg, 0.059 mmol) were added and purged with argon. The resultant mixture was stirred under argon atmosphere for 5 hours. The mixture was concentrated to residue. Residue was dissolved in ethyl acetate, washed with water, brine and dried over sodium sulfate and concentrated to get solid which was further purified on column (SiO2) using 15% ethyl acetate in hexane as eluent. This afforded 1.2 g (crude) of the pure compound.

Workup

  1. customthe resultant mixture was purged with nitrogen gas
  2. custompurged with argon
  3. concentrationThe mixture was concentrated to residue
  4. dissolutionResidue was dissolved in ethyl acetate
  5. washwashed with water, brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customto get solid which
  9. customwas further purified on column (SiO2)

Sources & evidence

ORD record
ord-c6a1cba5708f4403b9ead3e340915243
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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